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HCID 86738432, compound → 2-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)-1H-indole

HRID 485315
Notes
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Reaction equation

HRID 485315 reaction equation
C1(N[N:8]=[C:9]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:13][O:14][C:15]=2[CH3:16])[CH3:10])C=CC=CC=1>O>[CH3:16][C:15]1[O:14][N:13]=[C:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:11]=1[C:9]1[NH:8][C:17]2[C:22]([CH:10]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 86738432HCID 86738432, compound

Product 1

HCID 128548642-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1350 grams of polyphosphoric acid at 100° to 110° C., there is added portionwise 89.3 g (0.307 mole) of 1-(5-methyl-3-phenyl-4-isoxazolyl)-1-ethanone phenyl hydrazone, while maintaining the temperature between 105° and 115° C. After addition is complete the mixture is stirred at 100° to 110° C. for 3 hours. The mixture is then poured onto ice and water and the resulting solid is filtered and washed with water. The solid is then dissolved in ether, washed with water, dried and evaporated partially and cooled in ice. The resulting solid is filtered and washed with cold ether to give 2-(5-methyl-3-phenyl-4-isoxazolyl)-indole; m.p. 145° to 146° C.

Workup

  • temperaturewhile maintaining the temperature between 105° and 115° C
  • additionAfter addition
  • filtrationthe resulting solid is filtered
  • washwashed with water
  • dissolutionThe solid is then dissolved in ether
  • washwashed with water
  • customdried
  • customevaporated partially
  • temperaturecooled in ice
  • filtrationThe resulting solid is filtered
  • washwashed with cold ether
  • Sources & evidence

    ORD record
    ord-970c7d19cec94f22acf1cd40528093f4
    Source dataset
    uspto-grants-1985_08
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US04536499

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes